A COMPOSITION SUITABLE FOR HAIR CARE

Abstract

The present invention relates to a composition suitable for treating hair comprising a polymer selected from the group consisting of a branched polylysine and a branched polylysine in which to 80% of the amino groups present in the branched polylysine are derivatized so that they bear one or two substituents, and comprising at least one surfactant. Furthermore, the present invention relates to a branched polylysine in which 1 to 80% of the amino groups present in the branched polylysine are derivatized so that they bear one or two substituents, wherein these substituents are acyl groups having 6 to 24 C-atoms. Furthermore, the present invention relates to the use of a branched polylysine or of the branched polylysine in which amino groups are derivatized or of the said composition for treating hair. Furthermore, the present invention relates to a process for treating hair comprising contacting the hair with a branched polylysine or with the branched polylysine in which amino groups are derivatized or with the said composition.

Claims

1. A composition suitable for treating hair comprising a polymer selected from the group consisting of a branched polylysine and a branched polylysine in which 1 to 80% of the amino groups present in the branched polylysine are derivatized so that they bear one or two substituents, wherein these substituents are selected from the group consisting of acyl groups having 6 to 24 C-atoms, substituents having the formula CH.sub.2CH(OH)R or the formula CHRCH.sub.2(OH), wherein R is an alkyl moiety with 2 to 20 C-atoms, substituents having the formula C(O)NHR, wherein R is an alkyl moiety with 2 to 20 C-atoms, substituents of the formula CH.sub.2CH.sub.2C(O)OR.sup.1, wherein R.sup.1 is an alkyl group having 6 to 24 C-atoms, substituents formed by the reaction of the amino groups present in the branched polylysine with polyisobutylene succinic anhydride (PIBSA), and mixtures thereof, and comprising at least one surfactant selected from the group consisting of an anionic surfactant, a cationic surfactant, a nonionic surfactant, a zwitterionic surfactant, and mixtures thereof. and optionally comprising one or more further cosmetically acceptable ingredient different from the branched polylysine, different from the branched polylysine in which amino groups are derivatized, and different from the surfactant.

2. The composition according to claim 1, wherein the polymer is a branched polylysine in which amino groups are derivatized, wherein the substituents are selected from the group consisting of acyl groups having 10 to 20 C-atoms, substituents having the formula CH.sub.2CH(OH)R or the formula CHRCH.sub.2(OH), wherein R is an alkyl moiety with 2 to 20 C-atoms, substituents having the formula C(O)NHR, wherein R is an alkyl moiety with 2 to 20 C-atoms, substituents of the formula CH.sub.2CH.sub.2C(O)OR.sup.1, wherein R.sup.1 is an alkyl group having 6 to 24 C-atoms, substituents formed by the reaction of the amino groups present in the branched polylysine with polyisobuthylene succinic anhydride (PIBSA), and mixtures thereof.

3. The composition according to claim 1, wherein the composition is suitable for cleansing hair or suitable for conditioning hair.

4. The composition according to claim 1 comprising 0.1 to 10% by weight, of the polymer, 0.1 to 30% by weight, of the surfactant, and 0 to 99.8% by weight, of the one or more further cosmetically acceptable ingredient.

5. The composition according to claim 1 comprising 0.5 to 1.5% by weight by weight of the polymer, 6 to 19% by weight by weight of the surfactant, and 0 to 93.5% by weight by weight of the one or more further cosmetically acceptable ingredient, or comprising 0.5 to 1.5% by weight by weight of the polymer, 16 to 24% by weight by weight of the surfactant, and 0 to 83.5% by weight by weight of the one or more further cosmetically acceptable ingredient, or comprising 0.5 to 1.5% by weight by weight of the polymer, 0.5 to 1.2% by weight by weight of the surfactant, and 0 to 99% by weight by weight of the one or more further cosmetically acceptable ingredient.

6. The composition according to claim 1 comprising not more than 5% by weight inorganic salt.

7. The composition according to claim 1 comprising 5% by weight sodium chloride.

8. A branched polylysine in which 1 to 80% of the amino groups present in the branched polylysine are derivatized so that they bear one or two substituents, wherein these substituents are acyl groups having 6 to 24 C-atoms.

9. The branched polylysine in which amino groups are derivatized according to claim 8 wherein the substituents are acyl groups derived from oleic acid.

10. (canceled)

11. The process according to claim 12 wherein the hair to be treated is damaged and wherein the treating brings about a hair repair effect.

12. A process for treating hair, comprising contacting the hair with a branched polylysine or with a branched polylysine in which amino groups are derivatized, as defined claim 8.

13. A process for treating hair, comprising contacting the hair with a composition of claim 1.

14. The branched polylysine of claim 8 in which 1 to 20% of the amino groups are derivatized.

15. The branched polylysine of claim 8 in which 4 to 20% of the amino groups are derivatized.

16. The branched polylysine of claim 8 in which the acryl group has 10 to 20 C-atoms.

Description

EXAMPLES

Methods and Definitions

[0053] Concentrations

[0054] % means % by weight, unless defined differently.

[0055] Degree of Branching (DB)

[0056] The degree of branching (DB) of branched polylysine is defined according to H. Frey et al., Acta Polymer., 48, pages 30 to 35 (1997) as

DB[%]=1002D/(2D+L)

[0057] wherein D denotes the fraction of dendritic units and L denotes the fraction of linear units in the sample that is concerned.

[0058] DB was determined by .sup.1H NMR.

[0059] Amine Number

[0060] The amine number (unit: mg KOH/g), also referred to as amino number, was determined by titration. It was determined as described in WO 2016/062578 according to the formula given on page 13 of WO 2016/062578: [0061] Calculation:

[00001]$\mathrm{Amine}.Math..Math.\mathrm{number}=\frac{\left(V_P-V_B\right).Math.t.Math.c.Math.56.1}{E}=\frac{\left(V_P-V_B\right).Math.t}{E}.Math.5.61$ [0062] with [0063] Amine number=Fraction of total amine, calculated as mg KOH/g [0064] V.sub.P=Consumption of standard solution up to the inflection point [nil] [0065] V.sub.B=Consumption of standard solution in blank value titration [ml] [0066] t=titer of the standard solution [0067] c=concentration of the standard solution [=, 0.1 mol/I] [0068] 56.1=molar weight of KOH [g/mol] [0069] E=weight of sample taken [g].

[0070] Average Molar Mass Mn (Number Average) and Mw (Weight Average)

[0071] Mn and Mw were determined by gel permeation chromatography as described in WO 2016/062578 (see page 12 of WO 2016/062578, wherein trifluoroacete means trifluoroacetic acid):

[0072] M.sub.w and M.sub.n were determined by size exclusion chromatography under the following con-ditions:

[0073] Solvent: 0. (w/w) trifluoroacetate, 0.1 M NaCl in distilled water

[0074] Flow: 0.8 ml/min

[0075] Injection volume: 100 l

[0076] Column material: hydroxylated polymethacrylate (TSKgel G3000PWXL)

[0077] Calibration: poly(2-vinylpyridine) standards in the molar mass range from 839 to 1.020.000 g/mole (from PSS, Mainz, Germany)

[0078] Polydispersity

[0079] PD is defined as PD=Mw/Mn

Experiments Carried Out

Example 1: Branched Polylysine 1

[0080] 500 g of a 50% aqueous solution of L-Lysine were placed in a 21 four-necked flask equipped with a stirrer, a condensation column, a thermometer and a nitrogen inlet. The L-Lysine solution was heated to the boiling point. Then the temperature of the external heat source was increased according to the following profile: 1 h at 150 C., 1 h at 160, 1 h at 170 and 1 h at 180 C. while water was distilled off. The pressure was then decreased to 200 mbar while the external heat source was maintained at 180 C. The reaction for circa 2 hours continued under vacuum (200 mbar). The reaction melt was cooled at 120 C. and dissolved in 234 g of water. The polymer was characterized by gel permeation chromatography, determination of viscosity, pH, solid content, degree of branching and amino number:

[0081] Mn: 2150 g/mol

[0082] Mw: 4110 g/mol

[0083] PD: 1.9

[0084] viscosity (25 C.): 200 mPas (Rheomat, dynamic viscosity 100*1/sec)

[0085] pH: 10-11

[0086] solid content: 50.5%

[0087] degree of branching measured by .sup.1H-NMR=0.25

[0088] amino number: 185 mg KOH/g for the solution (390 mg KOH/g of polylysine neat)

Example 2: Branched Polylysine 2

[0089] 500 g of a 50% aqueous solution of L-Lysine were placed in a 21 four-necked flask equipped with a stirrer, a condensation column, a thermometer and a nitrogen inlet. The L-Lysine solution was heated to the boiling point. Then the temperature of the external heat source was increased according to the following profile: 1 h at 150 C., 1 h at 160, 1 h at 170 and 1 h at 180 C. while water was distilled off. The pressure was then decreased to 200 mbar while the external heat source was maintained at 180 C. The reaction for circa 1 hour continued under vacuum (200 mbar). The reaction melt was cooled at 120 C. and dissolved in 242 g of water. The polymer was characterized by gel permeation chromatography, determination of viscosity, pH, solid content, degree of branching and amino number:

[0090] Mn: 1350 g/mol

[0091] Mw: 2590 g/mol

[0092] PD: 1.9

[0093] viscosity. (25 C.): 110 mPas

[0094] pH: 11-12

[0095] solid content: 49.7%

[0096] degree of branching measured via .sup.1H-NMR=0.24

[0097] amino number: 215 mg KOH/g (433 mg KOH/g polylysine neat)

Example 3: Branched Polylysine 3

[0098] 1700 g of a 50% aqueous solution of L-Lysine were placed in a 21 four-necked flask equipped with a stirrer a condensation column, a thermometer and a nitrogen inlet. The L-Lysine solution was heated to the boiling point. Then the temperature of the external heat source was increased according to the following profile: 1 h at 150 C., 1 h at 160, 1 h at 170 and 1 h at 180 C. while water was distilled off. The pressure was then decreased to 200 mbar while the external heat source was maintained at 180 C. and the reaction for circa 1+ hours continued under vacuum (200 mbar). The warm reaction melt was collected in an aluminum vessel. At room temperature, a solid material was obtained.

[0099] The polymer was characterized by gel permeation chromatography, degree of branching and amino number:

[0100] Mn: 2150 g/mol

[0101] Mw: 3650 g/mol

[0102] PD: 1.7

[0103] degree of branching measured via .sup.1H-NMR=0.28

[0104] amino number: 410 mg KOH/g

Example 4: Branched Polylysine 4

[0105] 1700 g of a 50% aqueous solution of L-Lysine were placed in a 21 four-necked flask equipped with a stirrer a condensation column, a thermometer and a nitrogen inlet. The L-Lysine solution was heated to the boiling point. Then the temperature of the external heat source was increased according to the following profile: 1 h at 150 C., 1 h at 160, 1 h at 170 and 1 h at 180 C. while water was distilled off. The pressure was then decreased to 200 mbar while the external heat source was maintained at 180 C. and the reaction for circa 2 hours continued under vacuum (200 mbar). The warm reaction melt was collected in an aluminum vessel. At room temperature, a solid material was obtained.

[0106] The polymer was characterized by gel permeation chromatography, degree of branching and amino number:

[0107] Mn: 2070 g/mol

[0108] Mw: 4070 g/mol

[0109] PD: 2

[0110] degree of branching measured via .sup.1H-NMR=0.3

[0111] amino number: 366 mgKOH/g

Example 5: Branched Polylysine Modified with Oleic Acid (Modification of 4.8% of the Amino End Groups with Oleic Acid)

[0112] 250 g of branched polylysine made according to the procedure described in example 2 (not dissolved in water) was melted at 120 C. and 26.37 g oleic acid were added under stirring. The pressure was then decreased to 200 mbar while the external heat source was maintained at 180 C. and the reaction continued for circa 1 hour under vacuum (200 mbar). At room temperature, a solid material was obtained.

[0113] The polymer was characterized by gel permeation chromatography:

[0114] Mn: 1710 g/mol

[0115] Mw: 2930 g/mol

[0116] PD: 1.7

Example 6: Branched Polylysine Modified with Oleic Acid (Modification of 10% of the Amino End Groups with Oleic Acid)

[0117] 50 g of branched polylysine, made according to the procedure described in example 3 (not dissolved in water) was melted at 120 C. and 10.25 g oleic acid were added under stirring. The pressure was then decreased to 200 mbar while the external heat source was maintained at 180 C. and the reaction continued for circa 1 hour under vacuum (200 mbar). At room temperature, a solid material was obtained.

Application Examples

[0118] The denaturation temperatures of human hair proteins were determined as described by Wortmann et al. (J. Appl. Polym. Sci. 48 (1993) 137) using a heating rate of 2K/min. Denaturation temperatures are expressed as T.sub.max, i.e. the temperature of the denaturation peak maximum. The higher this temperature is the better. In case of damaged hair this denaturation temperature is lower than in case of virgin, not damaged, hair. If the denaturation temperature of damaged hair can be increased by treating it with a hair care composition this indicates a hair repair effect. Table 1 summarizes the DSC-data obtained.

TABLE-US-00001 TABLE 1 DSC data on virgin hair, 3 times bleached hair, and hair that has been bleached 3 times and after this treated with an aqueous polymer solution having a polymer-concentration of 1% by weight. Appl. T.sub.max Example Sample [ C.] Comments 1 virgin hair 141.8 2 placebo 133.2 3 times bleached then treated with water 3 with 140.9 3 times bleached then treated with example 1 the polylysine of example 1 4 With 140.4 3 times bleached then treated with example 2 the polylysine of example 2 5 with 141.8 3 times bleached then treated with example 3 the polylysine of example 3 6 with 142.2 3 times bleached then treated with example 4 the polylysine of example 4 7 with 142.6 3 times bleached then treated with example 5 the polylysine of example 5 which is branched polylysine modified with oleic acid 8 comparative 138.9 3 times bleached then treated with example 1 linear epsilon-polylysine (from Zhengzhou Bainafo Bioengineering Co. Ltd.)

[0119] The results show that treatment with branched polylysine results in a repair effect. This repair effect is higher than the repair effect achieved with linear epsilon-polylysine (comparative example 1). The repair effect of branched polylysine modified with oleic acid (according to example 5) is the best repair effect achieved amongst all samples tested.

Examples of Formulations

[0120] The following formulations have been made. Their pH and their viscosity was determined.

Formulation 1: A Sulfate-Free Soft Shampoo

[0121]

TABLE-US-00002 INCI % % active matter surfactants Plantapon SF Sodium Cocoamphoacetate, 40.00 Sodium Cocoamphoacetate 4-8% Glycerin, Lauryl Glucoside 2-6% Lauryl Glucoside, Sodium Cocoyl Glutamate <2% Sodium Cocoyl Glutamate, Sodium Lauryl Glucose <2% Sodium Lauryl Glucose Carboxylate Carboxylate Arlypon TT PEG/PPG-120/10 0.50 Trimethylolpropane Trioleate, Laureth-2 Cosmedia Polyquaternium-37 0.10 Ultragel 300 Branched polylysine Polylysine 1.00 from example 4 Lamesoft PO 65 Coco-Glucoside, 1.00 Coco-Glucoside 0.2-0.4% Glyceryl Oleate Water, demin. Aqua ad 100 Citric Acid Citric Acid qs [0122] pH value 5.6 (measured with a pH-meter Schott Instrument Lab 850 at 22 C.) [0123] Viscosity 9028 mPas (rpm 60 s64-22 C.) (measured with a digital Brookfield viscometer, 60 rotations per minute, spindle no. s64, measuring temperature was 22 C.)

Formulation 2: A Mild Baby Wash

[0124]

TABLE-US-00003 INCI % % active matter surfactants Plantapon PSC Coco-Glucoside, 20.00 Coco-Glucoside 6-10% Disodium Lauryl Disodium Lauryl 1-3% Sulfosuccinate, Sulfosuccinate Glycerin Plantacare Cocamidopropyl 20.00 Cocamidopropyl 8.8-9.2% 2000 UP Betaine Betaine Decyl Glucoside 2.00 Decyl Glucoside 1.0-1.2% Lamesoft PO 65 Coco-Glucoside, 1.00 Coco-Glucoside 0.2-0.4% Glyceryl Oleate Gluadin WLM Laurdimonium 1.00 Hydroxypropyl Hydrolyzed Wheat Protein Branched polylysine Polylysine 1.00 from example 4 Water, demin. Aqua ad 100 Citric Acid Citric Acid qs [0125] pH value 5.6 (measured with a pH-meter Schott Instrument Lab 850 at 22 C.) [0126] Viscosity 4909 mPas (rpm 60 s64-22 C.) (measured with a digital Brookfield viscometer, 60 rotations per minute, spindle no. s64, measuring temperature was 22 C.)

Formulation 3: An Argan Oil Hair Conditioner

[0127]

TABLE-US-00004 INCI % % active matter emulsifiers Dehyquart A-CA Cetrimonium Chloride 1.00 Cetrimonium Chloride 0.2-0.3% Emulgade 1000 NI Cetearyl Alcohol, 4.00 Ceteareth-20 0.4-0.8% Ceteareth-20 Lipofructyl Argania Spinosa 2.00 Argan LS 9779 Kernel Oil Branched polylysine Polylysine 1.00 from example 4 Glycerin Glycerin 2.00 Water, demin. Aqua ad 100 [0128] pH value 3.8 (measured with a pH-meter Schott Instrument Lab 850 at 22 C.) [0129] Viscosity <100 mPas (measured with a digital Brookfield viscometer, 60 rotations per minute, spindle no. s64, measuring temperature was 22 C.)